Size matters: A cautionary tale

by borednhony

 Jack’s sex life had ground to a halt. His regulars up and gone, Grindr providing no relief. If only he were a bit bigger down there, this would all be so much easier. Stuck with just his hand and his trusty porn playlist, a message pops up…

Added: Feb 2021 Updated: 17 Apr 2021 4,649 words 6,300 views 4.9 stars (8 votes)

*
*Grindr Notification*

Looking4Top4Now: “You hung?”

Jack: “Average, but know how to use it”

That was five minutes ago now, no additional response came. Not that Jack was expecting one, this seemed to be the pattern for the last week since he’d been back on the app. Jack was pretty built, not competition status or anything, but he took care of himself. Good pec shelf, defined fuck-me-v, a sizeable ass for his shorter frame, just the right amount of hair to make him look more masculine before he hit bear. So of course he got a lot of interest. Taps lead to messages. They’d exchange two or three, then either ask this or ask for a pic. Either response garnered a block or a ghost, or worse they’d ask if he was down to bottom. Jack did not bottom, no matter how many compliments he got on his ass. If he was being honest with himself, he was slightly below average, but everyone lied a little about their size on the internet right?

It wasn’t like he was a bad fuck either… he always reminded himself, he had regulars. He wouldn’t even be on the apps right now, but his regulars all seemed to have fallen through recently. One moved away, another got a boyfriend, one ghosted him, and then there was Chase. Chase had probably been his favorite of the roster, cute twunk, a little dumb, but a huge ass. Chase had called his package “boyfriend dick” for the first month they fucked, not too big, not too small, just right to take on the reg, but after time he’d gotten less and less enthusiastic when they met up. Then less and less enthusiastic about meeting up. Finally, two weeks ago he’d hit Jack up with a, “hey this has been fun, but I think I’ve graduated to something bigger.” That was it, no messages since. That started the streak of two months without a fuck.

Jack was horny as fuck now, the last message from “Looking4Top4Now” broke the dam. Fuck it, another night of bating till he passed out. He whipped out the lube, popped open a playlist online and got to work. “Fuck, this feels so good,” he thought to himself hitting first edge, “why do I even want ass, this is so much better,” but the image of the two guys fucking on screen immediately reminded him why. He pushed the thought away and started to zone out on his cock, up, down, up, down, edge, break, up, down.

An hour in he was starting to shake with each new wave of pleasure that hit him. He was in the zone, his inhibitions and the thoughts of the start of the night gone as he focused on his own cock, the short stroke from top to bottom and back. He was fixated on one of his favorite vids, an interracial fuck where both the top and bottom had giant cocks. There was something entrancing about watching the bottoms cock flop around, flinging pre-cum as the top rearranged his guts. And the moaning, fuck they were both so loud.

Right in the middle of this, as he was starting to think he might want to unload to this vid in particular, a window popped up in the middle of the screen. What the fuck, this site had tons of adds on the sides, but it never had pop ups. Without reading it he moused up to click the x. Nothing, the fucking button didn’t even highlight, ughhh. His frustration built, he was so ready for this release. Looking back at the center of the screen, as the sound of the amazing fuck now hidden continued playing through his head phones it read.

“Too small to get their attention?”

What the fuck, targeted ads based on Grindr convos, that was creepy. As soon as he read the sentence though it faded into another…

“Tired of conversations not leading to ass, of the ass you had locked down vanishing without a trace?”

Okay where was this going, was there going to be some stupid trick behind this. He tried to open a new tab to find the vid again, but realized his computer seemed to be frozen. The video was still playing loudly, but it wasn’t registering his clicks on or off the browser.

“Told yourself, it’s the motion of the ocean, not the size of the boat, one too many times…?”

Okay, that was a little creepy, that was exactly what he always said. He hadn’t stopped pumping his cock, not wanting to lose the edge, making it a bit hard to focus on how the message would’ve known something like this.

“Give us a try Jack…”

He almost jumped at this change. His heart racing at the idea that it knew his name. Was that sort of info that easy to find now… probably.

“A bigger cock is just a click away.”

Oh, of course, it was some stupid supplement or some pump or whatever. Not that he hadn’t tried both before. But a button finally appeared under this message in the window. It just said ‘Order Now.’ Ughhhhh he just wanted to get back to his porn already. He moused up and clicked, since it was apparently the only place that he was able to click on the screen.

A new window opened up with a short form to fill out, just his address and a check box. No credit card info? Okay fine, if this got him back to the other vid then whatever, not like they couldn’t find his address online anyway. He filled it out one handed as he kept pumping his cock in the other, having to pause as a few particularly strong waves of pleasure hit him from his edge, a little precum squirting out on his abs. He moved down to click ‘order’, but it wasn’t highlighted. Realizing he’d forgotten the check box he read the text next to it,

“I accept the risks and rewards of this order as my own, and hold no fault to the manufacturer or producer of my trial.”

“Ugh, whatever, just let me get back to the porn.” He clicked it and hit the order button. The form vanished, leaving the dialogue box.

“Thank you for your purchase, we promise you’ll regret it.”

Wait, what? He went to reread the message, figuring horny brain had just caused a mental typo, but it vanished. His computer was back to normal, his vid just reaching the climax as he was sucked back into the moment. The bottom was on his back, cock reaching past his belly button. Right as Jack’s focus returned, the whole bed the two actors were on moving as the top got rougher and rougher, the bottom’s cock erupted. This was his favorite part, the load from the bottom splattered over his head, then onto his face, his pecs, shot after shot. The site, and the moans were enough to send the top over the edge. His thrusts lost their rhythm as his orgasm hit him, a picture in picture showed the underside of the fuck, the tops chicken egg balls drawn up against his shaft, the hole and cock contracting as he fired his massive load into the bottom. The combination of this was more than enough and Jack erupted with him. He couldn’t reach his pecs, but his furry stomach was quickly coated in his spunk as he couldn’t help but let out a moan of his own. “Fuck that was a good one,” he thought, just glad the stupid pop up hadn’t ruined his fun for the night.

He stood, stretched, some of the cum dripping from his body and the tip of his cock onto the hardwood floors below as a yawn over took him. He cleaned up quickly, closing the screen as the next vid already started playing and made his way to bed. Outside his apartment door, an unmarked parcel had already arrived, waiting patiently for the morning.
Jack woke up the next morning before his alarm. Groaning as he checked the time on his phone, he rolled over to groan into the pillow, immediately feeling his modest morning wood press against the mattress.

“Ugh, fuck, I just jerked off last night, come on man,” he grumbled, not quite able to stop himself from grinding it against his bed, his boxers still on the living room floor after last night’s bate. After a few minutes of absent, lazy thrusting, the sun peeked through the blinds and Jack knew he wasn’t going to get back to sleep. Standing up finally, he stretched, ignoring the precum seeping into his sheets. He did a quick body check in his mirror, turning side to side to check out his hard work, little boner bobbing with his movements till he finally took it in his hand. The four inches throbbed, his tight little balls pulled up against the base, barely grapes under the meager shaft. “You know the drill buddy, no fun till after my run.” He tossed on his running shorts and a tank top, already imagining the feeling of going commando on the run as he stretched and grabbed his water bottle.

Exiting his apartment, Jack heard another door open, he and his neighbor Danny across the hall leaving at the same time. Danny smiled and gave a little wave as he turned to lock his door. Jack had had a bit of a crush on Danny ever since he’d moved in six months back. Danny had been in the apartment complex for a few years already and had brought Jack a welcome gift of wine on his move in day, after which he’d offered to help Jack carry his boxes up the stairs. Given Danny’s heavy muscular physique, easily twice Jack’s size at the same height, Jack took the bigger man up on his offer. Now as their eyes locked for that brief moment as Danny turned, Jack felt his stomach flutter again. Danny was in his classic plaid button down, sleeves rolled, red chest hair poking out of the top lending to the notion that the carpet likely matched the drapes, his beard neat and trimmed, short hair combed and clearly just out of the shower. Jack had never seen Danny on any of the apps, but knew he was somewhere on the gay side of the spectrum from the men he’d brought home. Jack had spent more than one evening jerking hard to the sounds of fucking happening on the other side of his bedroom wall, but that also meant that Danny was a top (if the always prominent bulge in anything he was wearing didn’t already give that away). Jack figured that would never work. So, he always kept their interactions friendly, and for once was glad his own wood was easier to hide. He stepped forward to actually say good morning, and in the process tripped over something set outside his door. He went tumbling forward and would’ve hit the hard ground between their doors but Danny was turning back around. He caught Jack in those thick arms, and for a moment they just stared at each other in silence. Jack could feel his own heart pounding, and could swear that Danny’s was doing the same. He pulled himself together and stood up, “Fuck, sorry I uh…” he looked back at the nondescript cardboard box. “I totally didn’t see that, haha.”

“Well, good thing I was here, can’t have you getting injured before you even start your work out.” Danny grinned as they both went a bit red, having an awkward laugh. “Hey, if you’re free tomorrow, I was planning on having a few friends over. Maybe you can stop by?”

Jack went even redder before answering, “Uh… yeah I don’t think I have anything going on. Text me if I can bring anything and the time.”

“Awesome. I’ll shoot you the details later, I gotta run… I guess so do you.” Danny winked, looking Jack up and down before heading down the stairs and out of view. Jack let out a breath he didn’t realize he’d been holding and leaned against the wall. He could still smell Danny’s cologne from having that broad chest pressed against him, fuck why did the hot ones have to be tops.

He turned to lock his door, almost tripping over the package a second time, but managing just to kick it into the door. What the fuck was this? Picking it up there wasn’t a shipping label, and the cardboard was plain with no logos or titles… weird. Okay, just gotta check it out before the run, then back to business. He picked it up. It was fairly light and not too large, maybe 7 inches to a side. Closing the door behind him, Jack set it on the kitchen counter, grabbing a knife to undo the tape. Inside were rainbow colored backing peanuts, and digging through he found nothing but what looked like a vitamin supplement bottle and a thank you card. The bottle was unmarked, just plain white aside from a little embossed ‘30 day supply’ near the bottom. Lifting the card, he read: “Thank you for your order. We hope you’ll enjoy your new endowment. Feel free to pass us around.”

What the fuck? How had this already gotten here? Plus he didn’t remember putting in his address, so that was a bit creepy. Jack’s wood had gone back to a semi as he’d opened the package, and he looked down at his non-existent bulge. It was probably bull shit, and he didn’t get a notification of his card getting charged… even if it didn’t work the strangeness of it all would make a good bar story, right? Ugh, fuck it. He opened up the bottle, the scent of jizz hitting him immediately causing him to pull it away. Cautiously he shook a couple pills out onto his hand. They even sort of looked like they were filled with cum, liquid gel capsules willed with a milky white, opaque substance…huh. He looked back at the card and dug through the packaging again to see if there were any instructions, but none were evident. Well… down the hatch. He popped the two pills into his mouth and swallowed with his water bottle, then stood still waiting to see if anything happened. After five minutes of standing, staring blankly at his kitchen counter, he reasserted that it was all some stupid joke or bizarre advertising campaign and decided he might as well get his run over with.

Even being mid-April, the morning was warm and humid. Jack was sweating more than usual by the halfway mark 3 miles from his apartment, and his mouth still tasted like cum from the pills. He stopped to catch his breath and try and wash some of the taste out at his favorite lookout point. His apartment wasn’t too far from a beach, and the hilltop crested to an amazing view, though whether he considered that view the ocean or the sunbathers depended on the day. It was earlier in the day than most people usually favored for a beach trip, and there were few people on the sand. One in particular caught his eye. He was a Latino guy with one of the best asses Jack had seen in or out of porn. Even from a distance Jack recognized that backside, as the guy lay on his stomach, the speedo doing nothing to cover the bottom thirdof his rear endowment. They’d talked on Grindr a few times now, but the last conversation had ended with Jack’s 4” dick pic and no response. Jack absently reached down to adjust himself remembering the shots he’d gotten form the guy before the conversation ended. Fuck he must be over heated, his balls felt so much lower than usual as he shifted them. Maybe it hadn’t been a good day to go commando after all, but he was feeling confident. It was barely another quarter mile down the hill before he hit the sand. He’d scrolled back through his messages to find the guys actual name, ignoring the buzzing in his groin as he tried to fight down the memories of arousal. It was weirdly intense today. Ah, found it: “Guillermo, but you can call me Will.” The other sun bathers were far enough away to be out of earshot here. Using the boldness he’d mustered, Jack plopped himself down in the sand next to Will’s towel, “Morning Will, been a while.”

Will looked up over his sun glasses, his dark hair still wet from what must’ve been a dip in the waves earlier, his skin glistening as the water slowly dried on his back and legs. “Do we… know each other?” The boldness already seemed to be paying off as the younger man’s eyes worked their way over Jacks body pausing at his exposed arms, then going wide as they traced down his crotch.

“Not sure if you’d remember me, we chatted on the app a few weeks ago.” Jack tried to keep it casual but felt his blood pumping lower now.

“Weird, I feel like I’d remember those.” Will smiled, his eyes still on Jack’s crotch, leading Jack to look down and see that he was right, fuck his balls were hanging out of the leg of the running short and they looked… big. Gone were his little grapes, replaced by chicken eggs and that feeling of pulsing and tingling he’d written off as runners high intensified.

“Oh fuck sorry, guess they popped out to say hi too.” He quickly tried to tuck them back into the leg hole, flushing as he felt them fall back out, this time hitting the sand. His cock surged forward between the embarrassment and the reaction to it, feeling tight in his shorts now. Will saw Jack’s expression, and his smile grew. The embarrassed ones were the cutest.

“Leave ‘em out, no one around to see them but me, and I don’t mind.” Jack could see Will’s ass flex in the skimpy briefs, which only worsened his situation as he tried desperately not to look at either the ass or his own crotch. Fuck this was a bad idea. “Though, if you wanted to show me more somewhere a little more private… I wouldn’t be opposed to that either.” Will pushed himself up on his arms now, back arched as his legs and crotch remained on his towel. “I life guard here sometimes, but it’s so early that no one’s going to be on duty.” He cocked his head towards the vacant life guard tower a few yards behind him.

Jack watched Will stand, and followed suit, unable to tear his eyes off that gorgeous ass walking in front of him to look at his own tent. Had he, he would’ve seen that where he usually stuck straight out, the little dick not big enough to curve along his hip, that’s exactly what it was doing. Each step, each heartbeat, his tool was snaking its way up his pelvis. From the time he’d started his run till now, he’d gone from his meager 4” pencil dick and was entering the life guard shack with 7” nearly reaching his hip as it throbbed, thickened, his balls churning as they over produced. As he entered the darkened room, Will closed the door behind him, and seeing Jack’s nervousness, pressed him up against the door. He pressed his lips to Jacks, their tongues immediately meeting, Will’s mouth tasting of his morning coffee and the salt air from the beach. Jack started to go weak in the knees. It’d been so long since he’d fucked, and he’d wanted it so bad it was surreal to have it handed over so easily.

Will ground their crotches together, and Jack felt that the big assed bottom in front of him was packing something hefty as Will took Jacks hands and placed them on his ass. Jack got the hint. He grabbed the big pillowy cheeks and the kissing intensified. This was real, and he was going to fucking enjoy every second of it. He pushed back against Will, both of them stumbling across the shack until Will’s ass hit the desk at the other side of the room and he hopped up onto it, not breaking the kiss as he wrapped his arms around Jacks body, pulling them close again. Jack standing between Will’s open legs now, just two layers of fabric separating their sex as he bit Jack’s earlobe softly, whispering, “I want that monster in me now.” The word immediately took Jack out of the moment, was he getting teased? He wanted Will, but what was this guy expecting?

Though he was momentarily distracted, Will was not. He reached down and in a fluid motion is speedo was on the floor, bare ass making the desk creak between their motion. Another second and Jack felt his running shorts drop, and the unfamiliar sensation of his cock springing up to hit him in the belly. He tried to look down to see what had happened, but Will wasn’t letting him break the kiss. Will adjusted, shifting himself forward on the desk and leaning back till his hole was just over the edge. He was hungry and didn’t want any foreplay getting in the way of filling his hole. Reaching between them, Jack felt Will lining up his throbbing shaft against the warm pucker of his ass. Will’s hand no longer took up the whole length of his shaft, and he could distinctly feel inches on either side of it left untouched. He couldn’t process what this meant, but it made him throb and he felt something wet leaking on to the tip of his dick. The smell of cum immediately filled the room as he realized, Will already took a load this morning and was using it as lube to take Jack’s dick.

Before he could think twice about that, Will slid forward on the desk and his cock was engulfed in the tightest, warmest hole he could remember having. Usually with bottoms, it felt good, but they’d never been truly tight for him. This felt like fucking a virgin and his cock throbbed hard. “Oh fuck baby, go slow, I’m not used to something this big.” Will moaned before pulling Jack against his chest, the kiss getting deeper and deeper. Jack flexed his cock, unbeknownst to him now approaching 8” rapidly, his girth twice what he started with as it outpaced the length. He began thrusting slowly, feeling his cock coated in the cum from Will’s last fuck, making each thrust a little easier than the last till they started to find a rhythm. Will broke the kiss, unable to stop himself from crying out at the big cocks assault on his ass. He buried his head in Jack’s shoulder as Jack’s thrusting picked up speed, the desk creaking and hitting the wall of the shack with a rhythmic thud.

To Jack’s horror, as soon as he started getting into a full fuck he already felt the cum churning in his balls. After no ass for so long, one that felt this amazing, the knowledge that he was fucking another guys cum deeper into Will and the risk of getting caught fucking this stud inside the lifeguard tower were all more than he could handle. Barely a minute into the fuck Jack grunted and groaned, “Oh fuck, I’m gonna shoot.”

He was too distracted between the feeling and the embarrassment to think how Will might react, but in response he heard the bottom yell, “Oh fuck yes baby, fill me up, give me all you got. I want that fucking load.” That was all he needed. He slammed his newly huge member balls deep inside Will, the coolness of the desks surface adding to the sensation of heat inside of the tight hole as he unloaded. His orgasm felt like it just kept going and going, and he thrust with it. His cock flexing as he shot what felt like the largest load of his life inside the insatiable bottom on the desk. About 30 seconds into the orgasm, he felt Will bite down on his shoulder and moan as his own load fired off, hitting Jack’s chest and abs and rolling down his torso. A minute later, the orgasm subsided but they were still pressed against each other panting, dripping sweat in the unventilated shack.

“That was…” Will started.

“I’m sorry it was so fast.”

“No, fuck no, don’t apologize—that was amazing. I don’t think I could take that thing for much longer. My ass is totally wrecked.” Will grinned. “Maybe with some warm up next time you can give me a full session, but that was… fuck that was perfect.”

Once they’d caught their breath, Jack started to pull out. “Slowly!” Will yelped, and Jack complied as he looked down at the thick shaft sticking out of that perfect ass. He stepped back and it just kept coming out, every time he expected to see his cock head there was just more shaft. His eyes went wide, when finally he felt the pressure of his mushroom cap against Will’s hole. He pulled, eliciting a moan from Will as the big head popped out of his hole followed by a torrent of cum onto the desk. Fuck he’d really shot a ton. He couldn’t look away from the site of his now 9” porn-star hole destroyer and the mess he’d caused inside Will, but the bottom was feeling more clear now that he wasn’t stuffed.

Will hopped off the desk, clenching his hole so as not to let anymore of the copious cum slide out. Though after a cock like Jack’s that was only now partially successful. He kissed Jack on the cheek as he pulled up his bathing suit. “We should go before the lifeguard actually does show up.” He winked again and grinned at Jack. That smile made Jack’s deflating cock twitch again as he pulled up his running shorts, having to adjust again so his low hangers weren’t dangling out the leg. No more commando running for him apparently, but how the fuck was this possible? The pills actually worked…

As they exited the life guard tower, back onto the beach as more people began to filter onto the cool morning sands, Will turned to Jack and said, “Give me your phone.” He took it, and put his number in, shooting himself a text so he had Jack’s too. “Call me sometime, I’d love a replay.” He got on his toes, giving Jack a last kiss on the cheek before going to gather his towel and bag.

Jack stood stunned for a moment, but the only thing to do was try and figure out how this all worked… and maybe put it to use some more. He figured the jog home might clear his mind and took off his shirt to run the 3 miles back to his apartment. He felt a new heaviness with each step as his package bounced in the running shorts, and the occasional coolness of the air every time his sack slipped out the leg.

Update posts:
Weekly Update: 6 March 2021Weekly Update*: 17 April 2021

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